


Holiday Dreams

by fangirlingtodeath513



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bed & Breakfast, Blow Jobs, Christmas, Christmas Fluff, Hand Jobs, M/M, Minor Castiel (Supernatural)/Other(s), Minor Rowena MacLeod/Sam Winchester, Miscommunication, Misunderstandings, New Beginnings, Past Relationship(s), Weddings
Language: English
Status: Completed
Published: 2020-01-12
Updated: 2020-01-12
Packaged: 2021-02-27 07:55:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,289
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22223677
Author URL: https://archiveofourown.org/users/fangirlingtodeath513/pseuds/fangirlingtodeath513
Summary: Ten years ago, Dean Winchester disappeared from Castiel's life without so much as an explanation. Now, he's sitting in the living room of Castiel's B&B with his younger brother and it digs up a lot of the feelings he never actually sat down and worked through.Dean Winchester never expected to see the love of his life ever again, not after he'd so royally screwed everything up with his irrational fears. He'd give anything to take back that one stupid decision.Can a late-night chat, some holiday magic, and a wedding bring these two back together?
Relationships: Castiel/Dean Winchester
Comments: 9
Kudos: 146
Collections: Destiel Harlequin Holiday Cheesefest Challenge 2019





	Holiday Dreams

**Author's Note:**

> Heyyyy there :D Back again with a Harlequin, this time for the Cheesefest holiday mini bang! As always, thank you to the lovely mods for putting this together and giving us such fun prompts to pick from.
> 
> Huge thank you to my awesome friend [Gii](https://archiveofourown.org/users/heylittleangel/pseuds/heylittleangel) for beta reading this fic for me! 
> 
> Hope you enjoy!

Dean’s not really a bed & breakfast kinda guy, but his little brother’s bachelor party isn’t something he’s gonna miss. As best man, he’d been in charge of planning it. He’d  _ wanted _ to plan a trip to New York City for expensive dinners and as many drinks as they could find, not to mention the line of bars and gentlemen’s clubs they could’ve gone to. Sam had vetoed that idea almost immediately, though Dean had sort of been expecting that.

That’s why, instead of that, they’re pulling up to a secluded B&B outside of Hartford, Connecticut. It’s a hell of a drive from where Sam and Rowena live, but Sam’s been talking about this place for years. It had taken a good amount of sweet-talking to get enough rooms for all five of them, but everyone’s got their own rooms and, by the look of the place, said rooms will be comfy as hell.

The B&B itself is a huge, white, Colonial-style house with a wide, wrap-around porch that lines the entire first floor of the house. The porch is dotted with chairs and benches and a couple of swings that look like they’d be nice in the morning with a cup of hot coffee. 

“I still can’t believe you got reservations here, Dean.” Sam shakes his head as he looks up at the building in awe.

“Yeah, well,” Dean says, shrugging. “I know you’ve been dying to come here, what better time than before you’re off the market for good?”

Sam snorts. “Been off the market for a while, but I appreciate the sentiment.”

Dean smirks, climbing the three steps up to the porch with his suitcase, hesitating for a moment. He’s not sure if he’s supposed to knock or just let himself in. He’s saved from having to make a decision when the door swings inward to reveal a short, blonde man with a welcoming grin.

“You must be the Winchester party. I’m one of the owners, Gabriel.” He holds a hand out to Dean, who shakes it with a small smile. “And you must be the man of the hour,” Gabriel says, shaking Sam’s hand. “Sam, right?”

“Yeah, nice to meet you.”

Gabriel sweeps an arm toward the door. “Please, come in, let’s get you all situated.” 

Dean lugs his suitcase inside, followed by Sam, Kevin, Garth, and Brady. Dean’s still not really pleased that Brady was invited, but Sam had insisted. Dean can’t stand the guy—he’s creepy as hell and something about him just seems… off. This is Sam’s bachelor weekend, though, so Dean’s prepared to suck it up and get along for Sam’s sake.

“So I’ve got you all on the top floor together. Sam’s got the biggest room at the end of the hall, three A,” Gabriel says as he doles out the keys between the five of them. “Why don’t you go ahead and get settled? My brother, the other owner, is getting a welcome snack together at the moment, which will be right in the sitting room through this door.” Gabriel gestures to the door behind himself that leads to a brightly-lit room with a large coffee table and comfortable chairs.

The five of them file upstairs and disperse to their separate rooms. Dean’s in the room closest to Sam’s, which has to be the second largest room on the floor. There’s a four-poster king-size bed in the center of the room and a door off to the left that leads to an attached bathroom, complete with jacuzzi tub. There’s a small fireplace on the right side of the bed with a fire roaring inside and small Christmas decorations dot the room. The thick comforter and flannel sheets look like a cloud and he’d give anything to fall into them and take a nap, but he’s sure he’ll have to make an appearance for that welcome snack thing—Sam would never let him pass on it.

He pulls a warm, clean sweater from his suitcase and changes into it before heading downstairs. The rest of the bachelor party is already in the sitting room with slices of pie in front of them. That, combined with the mouth-watering smell of fresh coffee, has Dean walking into the room before his eyes can comprehend what he’s seeing. There, filling Sam’s cup with steaming coffee, is none other than Castiel Novak, the man he’d ghosted nearly a decade ago. Dean freezes in the doorway and it feels like everything that happens next happens in slow motion. Sam raises a hand to wave at him and every set of eyes in the room turn to him, including Castiel’s bright blue ones. It’s the color Dean’s never been able to forget and now, seeing Cas standing in front of him like this? It’s too much. He spins on his heel and flees up to his room before anyone can even say anything, content to hide there for eternity.

***

Castiel watches him disappear with a mix of confusion and anger. Of all the people to come to this secluded B&B, of  _ course _ Dean Winchester would be one of them. It’s just Castiel’s luck. Still, he’s got a job to do, so he resumes filling Sam’s cup with coffee.

“What, uh… what was that?” Sam asks, eyes flickering between Castiel and the doorway where Dean had previously been.

Castiel smiles tightly. “Dean and I used to… know each other. It didn’t end well. It was years ago, though, it won’t be a problem for me.”

He hopes his pause wasn’t noticed by anyone. He remembers Dean admitting that he wasn’t out to his family and despite what Dean did to him, he doesn’t want to out the man before he’s ready.

“Oh shit, wait,  _ you’re _ Cas?  _ The _ Cas? I thought you were a woman this whole time!” Sam gapes, coffee entirely forgotten on the coffee table.

Cas raises his eyebrows. “ _ The _ Cas? What do you mean?”

Sam runs a hand through his hair, leaning back in his chair. “Like, a decade ago, Dean came and stayed with me for… I don’t know, six months maybe? He was super depressed and all he’d talk about was how he fucked up his relationship with someone named Cas. I never got the full story but he was really upset over it.” Sam chuckles and Castiel already doesn’t like the hopeful glint in his eye. “Small world, huh?”

“Indeed,” Cas mutters, grabbing the empty coffee carafe and retreating to the kitchen. 

Dean Winchester is the  _ last _ person Castiel ever wanted to see again, especially after what he’d done. Castiel had been left with a broken heart that had taken him years to repair. It had left him relationship shy, so he’d become exactly what he always thought Dean was—a guy sleeping around to avoid emotional intimacy issues. As a matter of fact, he’s supposed to be meeting Balthazar later tonight to hook up and now he can’t wait. Balthazar is always down for some rough hate sex and Cas has a lot of hate to get out, now.

He pushes himself to finish out the day. Luckily, Sam’s party hadn’t arrived until a few hours before dinner, which was Gabriel’s territory. He waves goodbye to his brother shortly before six and heads for the bar he’s meeting Balthazar at.

They end up getting drunk, so they’re forced to walk back to the B&B. Cas fumbles with the key for a moment before getting the door unlocked. The house is quiet but still softly lit by all the Christmas lights and decorations. There’s a fire burning itself out in the main living room but Balthazar breezes right by everything. He heads straight up to the fourth floor where Gabriel and Castiel’s bedrooms are, beckoning for Castiel to follow. He falls into step behind Balthazar and doesn’t waste a moment getting lost in the other man’s touch.

***

Dean can’t sleep, of course. His brain won’t stop churning long enough to get some sleep. So, instead of laying there staring at the ceiling, Dean pulls on a bathrobe and wanders around the cozy B&B. He heads upstairs first, mostly to assuage his curiosity. He’d seen there were four floors but Gabriel had referred to the third floor as the top floor, so what’s up here?

He’s faced with a door to his immediate left and a door at the end of the hallway. Both are marked with big, black ‘private’ signs, so Dean figures they must be Cas and Gabriel’s rooms. He’s about to head back downstairs when he hears moaning. He thinks it’s Gabriel at first, but no way. He  _ knows _ that moan. It’s haunted his dreams since he fled from Castiel’s apartment all those years ago. Castiel—prudish Castiel who lost his virginity to Dean at 22 and insisted that they always have sex with the lights off—is having sex?

Dean’s frozen to the spot. He knows it’s creepy and gross to listen to his ex-boyfriend fuck someone else, but he’s afraid he’ll be discovered if he moves. He’s probably not even supposed to be up here anyway. Decision made, he carefully makes his way downstairs and ends up in the kitchen. He’s not really sure he’s supposed to be poking around their kitchen, but this place doesn’t exactly work like a hotel, so maybe it’s fine. He finds some leftover pie in the fridge and cuts himself a slide, rummaging through the cabinets until he finds some hot cocoa mix.

A warm mug of cocoa in his hands, he tugs on his boots and coat and heads outside, parking himself on one of the swings. He pushes it idly as he eats his pie and sips his cocoa, watching the twinkling Christmas lights reflect off the snow blanketing the property. They’re only a couple of weeks from Christmas and just a week from Sam and Rowena’s wedding. He hopes the snow stays away for their sake so everyone can make it.

Halfway through his mug of cocoa, the front door clicks open and there’s a soft gasp behind Dean. He turns to find Castiel standing there in flannel pajama pants and a big, warm coat with a mug of something hot clutched in his hand.

“I’m sorry, I didn’t realize anyone would be out here, I’ll—” 

Dean cuts him off with a wave of his hand. “Your porch, Cas. I should get back to bed, anyway.” He collects his dishes and slips by Castiel into the house.

“Dean?”

He pauses, turning to look at Cas, who still has his back to Dean. “Yeah?”

“Why are you here?”

“Sam’s been talking about coming here for years.” Dean frowns, fork clattering against his plate as he shuffles his weight. “I didn’t know you were an owner, I swear. I wouldn’t have come if I did.”

Castiel’s head falls forward and Dean can just make out a soft chuckle. “I thought you were here to try and win me back.”

Dean’s brain whirs at that. Does Cas  _ want _ to be won back? Does Dean really still have a chance with him? “Is that… do you  _ want _ that?”

Castiel finally turns to look at him with a wry smile. “No. I’ve already made that mistake, I don’t need to make it again.” There’s an awkward pause where they just watch each other and then Cas draws in a breath and his eyes drop to Dean’s lips. “Although, since we’re both awake… the sex  _ was _ quite good…” Castiel trails off, taking a step toward Dean. Dean swallows, tongue darting out to wet his lips. Cas’s eyes follow the movement and Dean’s not quite sure what to make of that.

The tension snaps in half a second and Castiel’s lips are hot against his own, like a brand. He grasps the other man’s hips, dragging him as close as he possibly can. Cas’s tea clatters to the porch, splashing their boots with hot liquid. Dean doesn’t care, though. The two of them break apart and Castiel quickly cleans up the remains of the shattered cup as Dean collects his dishes and deposits them in the sink. Cas grips his wrist, leading him up the stairs and to the door of the room Dean’s staying in. Dean unlocks it quickly, gasping as Castiel kicks it shut behind them and shoves him against it. Then his lips are back on Dean’s, fingers fumbling with the tie of Dean’s sleep pants.

He’s already half-hard and having a hand so close to his cock has it filling out quickly. Cas smirks, biting at a sensitive spot on Dean’s neck as he shoves Dean’s pants and boxers down, quickly gripping Dean’s cock and giving it a few firm strokes. Dean’s head thumps back against the door as he groans softly. It’s so surreal to have Cas’s hand around his cock once more, but Dean’s not about to complain.

Castiel sinks to his knees and he’s not at all nervous like he’d been the last time they slept together. He’s confident and sure, tongue swirling around the head of Dean’s cock. Dean slips a hand in his hair, grunting softly as Cas swallows him down. 

  
“Fuck, you’re much better at that than I remember,” Dean breathes, eyes fluttering closed as Cas’s nose brushes against his stomach. Cas hums in response, throat working around the head of his cock as his tongue caresses the shaft.

He’s got Dean on the edge of an orgasm in only a couple of minutes, pulling away just as Dean’s thighs tense. Dean whines, eyes cracking open to look down at Cas. “W-why’d you stop?”

Castiel smirks. “You can come when I’m done with you.” He tugs Dean’s bathrobe and shirt off, nipping his ear. “That okay with you?”

Dean’s throat bobs as he swallows, nodding jerkily. “Fuck yes.”

Cas grabs his arm, redirecting him to the bed and pushing him down onto it, straddling his lap. 

“Aren’t you kinda overdressed?” Dean asks weakly, shivering when Cas leans down to kiss him.

“Not at the moment, no,” Cas murmurs against his lips, thumb brushing along Dean’s bottom lip. “Do you have lube or do I need to go get some?”

Dean squirms a bit. “Yeah, front pocket of my suitcase. Condoms, too.”

Cas slides off the bed gracefully, digging the small bottle of lube and a few condoms out of Dean’s bag. He drops his finds on the bed next to Dean, ripping one of the condoms open. “You’re still a switch?”

Dean nods dumbly, spreading his legs as Cas settles between them. It’s been a long time since he’s bottomed for anyone. Actually, now that he thinks about it, the last person he bottomed for was Cas… “I thought you didn’t like topping?”

“I don’t bottom anymore,” Cas says, sliding the condom over his fingers and slicking them with lube. 

Cas opening him up is surreal. The first and only time they’d done this, Dean had already prepped himself beforehand. Now, Cas’s fingers are gentle but sure as he stretches Dean open, stroking all the right places inside of him to leave him breathless.

“Cas, please,” Dean begs after a while, clenching around Cas’s fingers. He seems to get the hint, discarding the condom and grabbing a new one. He doesn’t even bother to undress, just tucks his pants—no underwear, but Dean’s brain refuses to comprehend that—under his balls and rolls the condom on. He drizzles some lube on his shaft, giving it a few quick strokes before pressing the head against Dean’s hole. Dean nods jerkily, biting down hard on his lip as Cas’s cock splits him open. He’s not entirely sure how thin these walls are and the last thing Dean needs is his little brother hearing them.

It’s unnervingly hot to watch Cas like this. He’s still fully clothed, hips grinding against Dean’s ass as he acclimates to the size. He’s older than Dean remembers, with wrinkles at the edges of his eyes and the perfect amount of scruff covering his jaw. Age has done him well.

Any other thoughts are quickly wiped from his mind when Castiel pulls out almost all the way and then thrusts back in roughly, his hips slapping against Dean’s ass with the force. Dean grunts, fingers twisting into the comforter below as Cas fucks him roughly.

Cas had  _ never _ been rough, he hadn’t even liked it when Dean was rough. Dean wraps his legs around Cas’s waist and lets him just take what he wants, content to just lay there and let Cas chase his own pleasure. Clearly, though, that won’t be allowed. Cas’s hands wander up Dean’s sides and skirt over his chest, pinching his nipples. Dean arches into the touch with a sharp inhale, eyes fluttering closed. Cas’s lips are on his then, warm and insistent and Dean yields immediately, sighing as Cas’s tongue sweeps into his mouth. He loops his arms around Cas’s neck, kissing him breathlessly as Cas continues to fuck him.

Eventually, Cas pulls away and snakes a hand down to Dean’s cock, giving it a few quick tugs as his thrusts grow more and more erratic.

“Come on, Dean, come for me,” Cas says, voice low and raspy. He twists his hand on the upstroke and Dean comes harder than he has in a long damn time, painting his own chest with cum. Castiel follows closely behind, hips jerking as he fills the condom with a quiet groan.

They stay like that for a moment, catching their breaths as they come down from the high. Cas pulls out after a moment and Dean winces at the loss, leaning back and watching as Cas discards the used condom and tucks himself away. He returns to the bed with a smirk, leaning down to kiss Dean thoroughly.

“Thanks, Dean. You’re as good as I remembered.” He starts to leave, which Dean’s sex-addled mind can’t comprehend. He leans up on his elbows with a frown.

“You don’t have to leave. You’re welcome to stay the night.”

Cas quirks an eyebrow at him, hand already gripping the doorknob. “I don’t sleep with my one-night stands, it tends to be a really bad idea. Goodnight, Dean.”

He’s gone before Dean can say anything else and Dean frowns at the door. He feels oddly used. Does Cas not  _ want _ him back? Why had he brought it up, then?

Shaking those thoughts away, Dean cleans himself up quickly and redresses. He doesn’t have time to dwell on that right now, it’s far too late and he’s got a busy day planned. Sighing, he curls up under the warm blankets and quickly falls asleep.

***

“You  _ what _ ?” Gabriel hisses, his pan of scrambled eggs forgotten on the stove. Castiel quirks an eyebrow, sipping his coffee.

“I slept with Dean.”

Gabriel stares at him with a mixture of horror and annoyance. “You can’t go around sleeping with our guests, Cas! Especially not ones who broke your heart a decade ago!”

Castiel rolls his eyes. “Yeah, a decade ago. I’m over it, have been for a while.”

“Oh, we both know that’s a bald-faced lie.” Gabriel points the spatula at him and a bit of partially cooked egg falls to the floor. “Stay away from him, Cas. If you fuck him over, it’ll jeopardize my business, the one I let you join after a certain someone broke your heart and made you swear off of love.”

Cas raises a placating hand. “I’ll behave, I promise. I know how much this place means to you.”

Gabriel nods, returning his attention to the stove. “Why’d you sleep with him, anyway? Thought you wanted nothing to do with him.”

“I thought so, too.” Cas sips his coffee, shrugging. “Kinda wanted to make him feel a little bit of what I felt when he left. Might’ve been a mistake, in hindsight.”

“A mistake?” Gabriel raises a curious eyebrow at him. “Why?”

Cas sighs, setting his mug on the table. “I think he may still have feelings for me.”

“So you _slept_ _with him_? I know you’re into this whole one-night-stand thing, so you should know better than to sleep with someone who’s got feelings for you!”

Cas fixes Gabriel with a glare. “I didn’t pick up on it until after. He invited me to stay the night.”

“Look, just…” Gabriel sighs and runs a hand through his hair, his entire body tense with what Cas can only imagine is stress. “Don’t fuck this up for me. That’s all I ask.”

Castiel puts his hands up placatingly once again, finishing up his coffee. He washes the mug quickly before heading out on his rounds, replenishing towels and toiletries in all of the rooms being used, except for Charlie and Dorothy’s room. They’re newlyweds and Cas isn’t about to disregard the “Do Not Disturb” sign hanging on the doorknob. He leaves them a note to come down to the front desk if they need anything and heads downstairs to get ready for the day’s check-ins. They’ve got four rooms checking in today. Castiel’s still not sure how Gabriel did all of this, but they’ve always been insanely busy year-round. Dean’s party had only gotten in because they’d had a wedding party cancel their reservations the day before Dean had called.

He spends almost all day thinking about Dean. He’s not sure if that’s a good thing or a bad thing. Despite telling Gabriel he’s been over Dean for a long time, seeing Dean had made it clear that was a lie. Seeing Dean after all these years brought up feelings Cas thought were long gone, replaced by anger and hatred. Apparently not.

Dean was the first person he’d ever fallen in love with. They were young when they met, barely twenty-one, and everything had moved so quickly. They were living together within six months and Cas was prepared to spend the rest of his life with Dean. 

He’d planned his first “I love you” perfectly. He’d made their favorite dinner and pie to celebrate. It was after they’d slept together that night when Cas finally got the nerve to say those words, whispered against the bare skin of Dean’s shoulder as they laid together. He’d thought Dean hadn’t even heard it at first, but then he’d leaped out of bed and pulled on his clothes, visibly shaking, before fleeing from their apartment.

Castiel still doesn’t understand it to this day. Dean hadn’t said anything, he’d just disappeared from Cas’s life in a matter of minutes.

He shakes those thoughts away as his shift ends. He’s supposed to go meet a friend at one of the bars in town but he’s really not feeling it tonight. He shoots them a text, canceling their plans, and heads for the kitchen. Gabriel’s already made dinner and he can hear the chatter from the dining room. He makes himself a plate as quietly as he can, creeping upstairs to his bedroom in peace.

He finds Dean alone in the sitting room late that night, close to midnight. Cas pauses in the doorway, contemplating whether to say something or not, but Dean spots him before he can decide. His mouth tips up in the barest hint of a smile, which Cas tentatively returns. There’s a tense silence between them before Cas steps into the room and clears his throat. “Why?”

Dean’s brows furrow, head tilted to the side as if to ask what Cas means.

“Why did you leave?” Cas tries again, watching with curiosity as Dean’s face falls. 

He picks at a loose thread on his shirt, steadfastly avoiding Cas’s gaze. “It’s a long story.”

Castiel raises his arms out to the sides before letting them fall back down. “I’ve got all the time in the world. And, frankly, you owe me an explanation.”

Dean huffs a quiet laugh, drawing his legs up onto the chair with him and wrapping his arms around them. The gesture makes him look like a small, scared little kid. “You’re right, I do. Um… my parents got divorced when I was in middle school. It was a really nasty divorce and I’d always thought they had the perfect relationship. Then we found out he had a whole other family in the next state. Kinda killed the idea of love for me,” Dean chuckles bitterly, angrily wiping under his eyes. “Then I met  _ you _ , and I… really liked you. Maybe even… you know. But you said it and my brain just kinda short-circuited, I guess? I freaked out and went to stay with Sam for a couple of days. By the time I realized how fucking stupid it was to be scared, you were already gone.”

Castiel smiles wryly. “I left the next morning to stay with Gabriel. Ended up just moving here to help him with the business. Needed a change.”

Dean nods, eyes downcast and shoulders hunched. “I know it doesn’t fix… well, anything, really, but I am sorry. It was so stupid and selfish and I never should’ve done that.”

“It’s fine.” Cas crosses the room, sitting across from Dean. “I worked through those feelings a while ago.”

Dean hums, pulling his sleeves down over his hands. “Right. Well, that’s… good.”

Cas rolls his eyes. He knows Dean well enough even after all these years to know he’s got something on his mind. “Just say it.”

“Say what?”

“Whatever you’re thinking. I know you’ve got something on your mind.”

Dean clears his throat, still carefully avoiding Castiel’s gaze. “I just, um… what you said last night, is there any chance of us… y’know?”

Castiel frowns. “Getting back together? Why would you want that?”

“I, uh… you were the best thing that ever happened to me. I know I fucked it up but… I don’t know. Forget it.” He starts to get up, so Cas shuffles forward and rests a hand on his knee to stop him. Dean stares at it for a moment before settling back in his chair.

Does he really want to do this? He’d been in love with Dean, sure, even pictured their future together, but it seemed like all of that had shattered the moment Dean walked out the door. They can’t just pick up where they left off, but maybe…

“I can’t trust you,” he starts, his entire chest aching when he sees Dean’s face fall. “Right now. I can’t trust you right now. What you did hurt, Dean. But… I could trust you again. If you wanted me to. If you tried.”

Dean looks up at him for the first time since they began talking and smiles slightly. “Yeah?”

Castiel smiles softly and nods, squeezing Dean’s knee gently before sitting back. “Yes.”

It’s like the tension ebbs out of him with his exhale. He looks far more comfortable than he’s looked since learning Castiel was here, and he’s even smiling slightly. It’s a smile Cas has missed all these years, though he never would have admitted that to anyone. “Um, I can’t really take you out to dinner or anything, at least not right now, but we’re going ice skating tomorrow night if you want to join us?”

“It’s your brother’s bachelor party,” Cas says with a laugh. “You don’t have to push your brother aside for me.”

Dean snorts. “It’s fine. He’s got his friends here and he’s… he knows. Well, some of it, anyway.”

Cas smirks. “Yes, he mentioned he assumed I was a female the entire time you talked about me.”

Dean laughs. “Yeah, no surprise there. I’ve been out for a while now but I’ve never actually brought a boyfriend around.”

“Why?”

He shrugs. “Never really had the opportunity, I guess. I wasn’t out until a year after… us. Haven’t really dated anyone since, actually. A couple of flings here and there but nothing serious.”

That doesn’t exactly help Cas trust him more, but he doesn’t really want to back out now. If he’s being honest with himself, despite how badly Dean hurt him, he does really want to give them another shot. “Nothing serious?”

Dean smiles a bit, as if he can see Cas’s line of thought, and shakes his head. “No, I spent longer than I’d like to admit caught up on you and how bad I’d fucked up and once I finally decided to get through it, I just kept comparing everyone to you.” He smiles wryly. “So maybe not as over it as I thought.”

Dean had been comparing people to him? That’s… not what he’d expected to hear. They’d had a good relationship, sure, but they’d fought over stupid things and they’d moved far too quickly. Cas had a habit of being a bit of a slob and the times Dean had exasperatedly told him to throw his dirty clothes in the hamper was innumerable. 

“Why do you look so surprised?” Dean asks softly, pulling his feet up onto the chair once again. This time he doesn’t look so small and sad though, just comfortable.

“I didn’t think you’d compare people to me. I’m just… average.”

Dean chuckles. “Cas, you’re far from average, believe me. I was a scared kid and I didn’t have a damn clue what I was doing back then, but I do now.” He frowns, tilting his head to the side. “Kinda. I hope. Whatever. Anyway, I know what I want and you’re it. I know I have to prove that and I’m fine with that. I’ll prove it.”

Cas sits back in his seat, eyebrows raised. “Well, I look forward to it.”

“So ice skating, then?”

Cas smiles. “Sure.”

***

Dean changes his outfit at least a dozen times before he finally settles on a flannel button-down, the pair of dark jeans that make his ass look fantastic, and a pair of leather boots. He fidgets with his hair for the better part of ten minutes and spritzes some cologne on before heading down to the lobby. He’s meeting the rest of the bachelor party there so they can all leave at the same time, but he’d told Sam to meet him there a few minutes early. He wants to run the whole situation by his brother and make sure it’s okay before he brings an unauthorized tag-along to his bachelor party.

“Dude, are you  _ kidding _ me? Of course you can bring him! I’m so happy for you, man!” Sam practically shouts when Dean tells him, dragging Dean into a bone-crushing hug. Dean huffs and wraps his arms around his brother. 

“Lower your voice, Sam, it’s just a date. I still have to prove that I’m not the same asshole I was back then. Congratulate me when I’ve done that.”

Sam smirks and lets him go. “Right, so that’s why you’re wearing cologne? I don’t think I’ve ever actually seen you wear cologne. You must really want him back.”

Dean shrugs, scuffing his boot against the hardwood. “Yeah. He’s… He means a lot to me. I didn’t think I’d get a second chance, I thought he’d just be the one that got away, but I’m not gonna fuck this up. Not again.”

Sam grins, clapping him on the shoulder. “Good. You should bring him to the wedding.” He throws his hands up in a placating gesture when Dean shoots him a glare. “If it goes well, I mean. It’s gonna go well, but you’re understandably nervous.”

Dean rolls his eyes. “You’re the one getting married, shouldn’t you be nervous?”

Sam’s grin widens and it’s almost sickening how in love he looks. “Nah, Rowena’s the one for me. Knew it the minute I met her.”

“She hated you.”

“Yeah, but look where we are now,” Sam answers with a shrug and a mischievous smile. “Besides, you know how persistent I am when I want something.”

Dean shivers. “Yeah, you’re right. Poor Rowena.”

Sam scoffs. “Yeah, yeah, whatever. Just go get your boy toy and let’s do this.”

He winces at the edge in Sam’s voice. “Look, I know how things went down last time we went ice skating—”

“Dean, relax, it won’t be like that.” Sam smirks and cracks his knuckles. “Because this time, I’m gonna whoop your ass. Rowena’s been teaching me how to skate better.”

Dean sighs and rubs a hand over his forehead. “Right, okay, well, I’m gonna go grab everyone and then we can get going. Just… dial it down to a seven, will you? I don’t wanna scare Cas off before I even get a chance to win him back.”

Sam grins. “No promises.”

Dean shakes his head and fixes his shirt collar as the rest of the group descends the stairs. Cas appears from the kitchen and they all head for the cars. Dean’s hand tries to search out Cas’s like it did so many times before when they were together, but he yanks it back quickly. That’s not his place anymore, at least, not yet.

The ice skating date goes surprisingly well. Dean and Cas are left with Garth, which is absolutely fine by Dean. Garth’s actually a surprisingly cool guy, despite his always constant peppiness. He and Cas get along almost instantly, which is definitely a plus, and they don’t have to race with Sam, thank God. That kid is far too competitive for his own good. 

It’s almost like he and Cas fall right back into the relationship they’d had before. They’re quick to make each other laugh and Cas still has the same dry sense of humor Dean had always adored. His smile still makes Dean’s heart skip a beat, especially when he gets laughing so hard that his nose scrunches. Dean thinks it might just be the cutest damn thing on the planet, though it’s a little early to start saying stuff like that, so he keeps it to himself.

“Hey,” Dean says as they head for the cars, falling behind the rest of the group. Cas keeps pace with him, reaching out to take Dean’s hand and give it a squeeze.

“Hey, yourself.”

Dean smiles and looks down at the ground for a moment before stopping and tugging Cas’s hand until the man faces him. “We’re heading back tomorrow night, but, uh, Sam’s officially given me permission to bring you to the wedding—uh, if that’s something you’d be interested in, obviously, you don’t have to—”

“Dean, whoa. I’d love to be your date.”

“Gabriel won’t mind?”

Cas snorts. “Gabriel was running the inn for three years before I came along, I’m sure he’ll manage. Besides, it’ll only be for the weekend, right?”

“Right,” Dean says, smiling softly as Cas squeezes his hand. “But if everything goes well..”

“Then we’ll deal with that when we get there,” Cas answers with a wry smile, shaking his head and pulling Dean toward the car. “We’ve got all the time in the world, Dean, no need to rush it.”

***

Dean adjusts his bowtie nervously, patting the pocket over his heart once again to make sure Rowena’s ring is still there. He’s petrified that he’s going to lose it and ruin the entire wedding.

“Here, let me,” Cas murmurs, stepping in front of Dean to straighten his bowtie. “There. You clean up nice, Winchester. Maybe we should get you in a tux more often.”

Dean laughs. “Yeah, we’ll see. I’ll take jeans and a flannel over a monkey suit any day.” He turns to scrutinize himself in the mirror, smoothing down a stray hair. “Do I look okay?”

Cas smiles and presses a kiss to his cheek. “You look dashing.”

Dean grins. “Dashing, huh? Very fairytale princess of you.”

“Well,” Cas says, lips tipped in a smirk as he draws Dean into a kiss. “I suppose you’ll have to be my knight in shining armor, then. Christmas is a good time for a fairytale, after all.”

A knock on the door startles them away from each other, sheepish and grinning. 

“I’ll be right out!” Dean calls, giving Cas one last quick kiss before he follows Kevin to where the rest of the bridal party has congregated. Everyone looks shockingly good and Sam’s beaming, not a hint of nervousness on him. It’s reassuring, to say the least. 

Dean shepherds everyone into the hallway five minutes before the ceremony is supposed to begin. They’d already gotten word from Rowena that she’d be ready on time, so by the time Sam heads into the room, Rowena’s rounding the corner in a gorgeous white dress. Dean’s gotta admit, his kid brother did pretty well for himself, Rowena’s a catch. He shoots her a grin and holds his arm out. “Still can’t believe you asked me to walk you down the aisle.”

Rowena chuckles. “Why? You’re important to Sam and I find that I don’t actually mind your company.”

Dean snorts. “Gee, thanks, you really know how to make a guy feel special.”

“Isn’t that your date’s job?” Rowena says with a sly smirk, face instantly smoothing as the wedding planner motions for them. Dean takes a moment to compose himself before they turn the corner and walk into the room. 

***

The rest of the wedding is a blur of speeches and dancing and photo opportunities. Finally, when Dean gets a moment to himself to just breathe, he finds Cas in the crowd and draws him into a tight hug, breathing a sigh of relief. 

  
“Your speech was cute,” Cas murmurs against his temple, hugging him just as tightly.

“Thanks,” Dean whispers back, smiling softly. He’d worried about that speech for months, but it seemed like Sam and Rowena had both liked it, so he was counting it as a success.

“I have a present for you,” Cas says, running his fingers through the short hairs at the back of Dean’s head gently. Despite not wanting to, Dean leans back to look at him.

“For me? Why?”

Cas smiles. “Call it an early Christmas present.” He lets go of Dean to dig around in his pocket for a moment before pulling out a small box with a bow on it. He holds it out to Dean, who takes it with a shy smile. He’s still got a week to get something for Castiel, technically, but he should probably get on that.

“Do you want me to open it now?”

“Up to you. It’s nothing inappropriate,” he says with a laugh that’s just a little bit nervous, slipping his hands into the pockets of his suit. 

Dean carefully tugs at the ribbon to undo the bow, tucking it into his pocket as he opens the box. There’s a key nestled inside, a rather plain silver one. There’s no note and it’s not one of his keys, so he looks up at Cas with a confused frown. Cas chuckles, though there’s a slight blush on his cheeks.

“It’s a key to my room at the B&B. I know we’re going to be long-distance, at least for a little while, so… you’ve got a key if you want to come visit.” He smiles wryly. “Just text me before you do so I can make sure there’s no dirty laundry lying around.”

Dean laughs, though it’s softer and more emotional than he means it to be. Cas trusting him with a key to his room is a huge step and it assuages his fear that he’s not actually redeeming himself. “I don’t care about your dirty laundry, but I will promise to text you before I come to visit.” He reels Cas in for a chaste but pleased kiss, brushing the pad of his thumb along Cas’s cheek. “Thank you for trusting me with this.”

Castiel smiles and presses a soft kiss to Dean’s lips. “Baby steps.”

***

It’s been two years since Cas gave him this key and Dean’s kept his promise. He’s  _ always _ texted Castiel before using it, and this is the first time he’s ever used it to sneak into Cas’s room uninvited. He figures his boyfriend will forgive him for this one, though. 

He has a giddy grin on his face the entire time he gets Cas’s room ready. He runs a bath and drops Cas’s favorite bath bomb in, carefully spreading flowers over the surface of the water. He lights a couple of Cas’s favorite candles around the room and sprinkles rose petals on the bed. He checks for the hundredth time that the ring box is still in his pocket and then he waits.

He hears keys jingling in the hallway not ten minutes later and, since Gabriel’s still downstairs for dinner, it’s gotta be Castiel. Sure enough, the door swings open and his boyfriend’s beautiful frame fills the doorway. He stops short when he sees Dean there, eyes darting around the room as he takes in the decorations Dean had painstakingly placed around—the candles, the rose petals on the bed, and the soft music floating from the bathroom. His keys clatter to the floor as his eyes refocus on Dean.

“You… I didn’t… you were supposed to text me,” Cas stutters out, though there’s no heat behind his words. He looks more shocked than Dean expects him to, though maybe he’s figured out what Dean’s here to do.

“I know, but I’m hoping you can forgive me for this one. I wanted it to be a surprise.” Dean clears his throat and picks Cas’s keys up off the floor, setting them in the dish by the door where he always keeps them. “So, um, I know we’re still working through some issues and we haven’t really figured out where we want to live yet or if you’re going to keep working here but I don’t care about any of that.” He fumbles in his pocket for a moment before producing the small ring box, holding it in his palm for a moment before dropping to one knee and flipping it open. “Look, I know we have a ton to figure out still and I know I still haven’t earned your full trust back, but I wanted to do something to prove to you that I’m in this for the long haul. Marry me?”

Cas blinks at him, opening and closing his mouth a few times before taking a step back. “You’re not just asking me to marry you to prove that, are you?”

Dean chuckles softly. “No. I’m asking you to marry me because I want to spend the rest of my life with you, wherever that is and whatever that looks like. Proving that I’m in this for the foreseeable future is just a bonus.”

Cas slowly breaks into a grin and drops to his knees to pull Dean into a fierce kiss. “Then of course I’ll marry you.” His eyes get a little watery as Dean slides the ring onto his finger and he sniffles. “Gabriel was betting you’d propose Christmas morning.”

Dean grins. “Well, we can tell everyone then if you want. I kinda just wanted this to be for us, though.”

“I love that idea,” Cas murmurs, drawing Dean into another kiss, this one soft and sweet. 

Dean smiles, brushing his thumb over the smooth metal on Cas’s finger. “Should we relax tonight? There’s a warm bath with your favorite bath bomb in it and I may or may not have picked up some massage oil.”

Cas grins. “Massage? You do have magic fingers.”

Dean smirks. “I’m sure there will be several uses for my magic fingers tonight.”

“Better be,” Cas answers with a small laugh, pulling Dean into another kiss. It’s warm and perfect and there’s nowhere else Dean would rather be in the world at Christmas, especially with the way the soft twinkling lights of Cas’s decorations light up his face. He’s more than ready to spend the rest of his life waking up to that face.

**Author's Note:**

> Find **me** on [Tumblr](https://fangirlingtodeath513.tumblr.com/) and [Pillowfort](https://www.pillowfort.io/fangirlingtodeath513)  
>   
>  **Please don’t post my works anywhere without my permission.**


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